This invention relates to novel N-(pyridinylaminocarbonyl)benzenesulfonamides. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, e.g., plant growth regulants and herbicides.
There are a number of references to compounds with the general formula: ##STR1## in the literature.
German Pat. No. 1,117,103 (Feb. 11, 1953) discloses ##STR2## as a pharmaceutical intermediate.
Logemann, W.; Caprio, W.; and Artini, D; Farmaco (Pavia), Ed. Sci. 12, 589 (1956) discloses the synthesis of ##STR3## which was treated as a hypoglycemic agent.
German Pat. No. 1,012,598 (July 25, 1957) discloses the following as blood sugar lowering and bacteriostatic agents: ##STR4##
Ruschig, H. et al., Arzneimitt-Foroch, 8, 448 (1958) reports on blood sugar reducing agents: ##STR5##
U.S. Pat. No. 2,977,375 (Mar. 28, 1961) and British Pat. No. 797,474 (July 2, 1958) disclose the same subject matter as in German Pat. No. 1,012,598 mentioned above.
Onishi, S., Yakugaku Zasski 79, 559 (1959) discloses the following, tested as hypoglycemics; ##STR6##
Holland, G. F., J. Org. Chem., 26, 1662 (1961) discloses compounds of the following strucutre tested as antidiabetics. ##STR7##
Brzozowski, Z., Zh. Obsch. Khem., 39, 430 (1969) discloses aniline complexes of the following: ##STR8## No use was disclosed.
Brzozowski, Z., Rocz. Chem., 43, 1761 (1961) discloses the synthesis of: ##STR9##
German Pat. No. 2,205,194 (Aug. 24, 1972) discloses cardiovascular, hypertensive analgesic and antiinflammatory drugs, CNS stimulants and antispasmodics. ##STR10## wherein R.sub.1 =alkylphenylsulfonamido;
R.sub.2 =H or alkyl; and PA1 R=H, carbamoyl, acyl, or arylsulfonyl. PA1 Y is CH.sub.3 --, CH.sub.3 CH.sub.2 --, CH.sub.3 O--, CH.sub.3 CH.sub.2 O--, Cl, Br or F; ##STR13## R.sub.1 is CO.sub.2 R.sub.4, CF.sub.3, NO.sub.2, Cl, R.sub.5 SO.sub.2 -- or R.sub.6 R.sub.7 NSO.sub.2 --; PA1 R.sub.2 is H, Cl or CH.sub.3 ; PA1 R.sub.3 is Cl; PA1 R.sub.4 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, ClCH.sub.2 CH.sub.2 -- or CH.sub.3 OCH.sub.2 CH.sub.2 --; PA1 R.sub.5 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.6 and R.sub.7 are independently CH.sub.3 -- or CH.sub.3 CH.sub.2 --; provided that PA1 when R.sub.2 is Cl or CH.sub.3 --, R.sub.1 must be Cl or NO.sub.2 ; PA1 when R.sub.1 is CF.sub.3, NO.sub.2 or Cl, then X and Y are independently CH.sub.3 -- or CH.sub.3 O--. PA1 (1) R.sub.1 is R.sub.6 R.sub.7 NSO.sub.2 --, R.sub.5 SO.sub.2 --, CO.sub.2 R.sub.4 wherein R.sub.4 is C.sub.1 -C.sub.3 alkyl or allyl, or; PA1 (2) R.sub.1 is NO.sub.2 and R.sub.2 is Cl. PA1 (3) Y is Cl, Br, CH.sub.3 -- or CH.sub.3 O--. PA1 (4) Y is Cl, Br, CH.sub.3 -- or CH.sub.3 O--.
Abon Ouf, A. A., et al., J. Drug. Res., 6, 123 (1974) discloses the following as being related to antidiabetic drugs. ##STR11##
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesirable vegetation is available; such materials are commonly referred to as herbicides. The need still exists; however, for more effective herbicides.